Billionaire
by Exquisiteliltart
Summary: Regina takes Emma out for a fancy date. Updated: chapter 3 on 8.26.12
1. Chapter 1

**Title: Fuck You Like a Billionaire (1/2)**

Pairing: Regina/Emma  
Rating: NC-17 (Smut, anal + toys, packing)…and Fluff! (Cause I love you!)

Disclaimer: These characters are not my creative property

Summary_:_ Anonymous asked you: prompt: swan queen anal sex + toys

A/N: First chapter is mostly fluff….Inspired by Peaches song "Billionaire." This is dedicated to Helebette.

_It don't even matter: morning moon light_

_And in spite of all the bullshit we been through_

_I will continue to fuck you like I like_

_Lick that pussy just right! ~ Peaches, Billionaire _

"You've displeased me, for shame!" Regina shook her head as she paced back and forth, but Emma could tell by the light in her eyes she wasn't exactly angry: Regina wanted something. She wanted something she couldn't bring herself to ask for outright, and so this was the routine they engaged in: Emma accepting a "punishment" (gladly) and Regina maintaining her pride. Emma had learned it was always best to play along rather than call her out. Putting a name to the game would result in actual anger. This little show was for promotional use only (not for resale).

"I'm sorry, you're right. I should have consulted you before I signed Henry's permission slip," Emma did her best to sound resolute and ashamed.

"Well, I accept," Regina breezily waved her hand through the air, "but of course, you will have to be punished as I see fit…tonight"

"Right, you'll punish me…heard that before," Emma wobbled her lips to ward away the smile that was threatening to break out. Regina's punishments were creative and weirdly sadistic, but not in a traditional way. Mostly, it was just so Regina could get her way without argument. Emma couldn't wait to find out what lay ahead.

"Should never have let her watch that Prom episode of 'Glee'…" Emma muttered as she struggled into the dress that Regina had waiting for her. After her 4pm hair appointment to get her "ringlets coiffed", nails polished, and make up done she was already regretting going along with Regina's whim. (A whim that was anything but, since Emma's various appointments had been booked, confirmed and paid for by Regina in advance.)

The dress was tight black satin, and she was already longing to get out of it before she had even put on the matching heels. Her punishment was a date with Regina; a fancy date at that. Who knew that Mr. Gold had a limousine rental service as one of his side businesses? The long black stretch was currently parked on the street and Emma was hurrying as best she could to get dressed and not keep Regina waiting.

The driver opened the door for her and she awkwardly crawled into the dark interior not used to navigating her space in a dress, (thighs together, Swan). And good god damned there was Regina: handing her a flute of champagne, smiling, and in black Tuxedo. Before Emma could catch her words Regina fashioned a red rose corsage to her wrist, which matched the boutonniere Regina had fastened to the breast of her suit. Emma smelled her rose and then leaned forward to share a kiss with her date. She was instantly struck by the pleasant smell of expensive men's cologne. Emma's throat went dry as Regina moved closer, their thighs touching as the limo drove off.

"You look..."

"Handsome?" Regina supplied tilting her head and smiling as if she was up to mischief.

"Yes," Emma breathed, although in her head it was more like an expletive squeal. Emma hadn't attended her high school prom on account of being knocked up and incarcerated, but even if she hadn't been she probably wouldn't have attended. Dancing slowly to "I'm Not in Love" with a sweaty palmed boy didn't strike a chord or have a place on her bucket list. However, Regina- a _woman_…her woman, dressed so fine and masculine and smelling so good in the back of a limousine was something she could definitely get on board with. Regina was always so mature and sophisticated in all the ways that Emma felt underdeveloped; this dynamic was actually what balanced the scales of their relationship.

Regina kissed her again, scratching lightly over Emma's chest, to feel her satin encased breasts. With devilish and deliberate intent, Regina took Emma's hand in her hers kissed her knuckles individually and then in a maddeningly slow manner led Emma's hand over her thigh and up. Emma's eyes widened as Regina laughed in that way of hers that sounded oh so cute and oh so evil.

"What's that?" Emma asked in faux innocence.

"My desire, dear," Regina said in her old school way that would have sounded super dorky were it anyone else. Emma kind of thought it felt like a rolled up scarf in all actuality, but she was in no position to contradict. If she played her card right she'd be in many positions come night's end.

Emma would have preferred to have dined at "Captain Jimbo's Bodacious Beef Buffet", but Regina insisted on the Crème de la Crème and so they were shown a table at "Cecaelia" a 5 star seafood restaurant.

All eyes were on the couple as they walked hand and hand through the restaurant to their seats. Regina acted the perfect gentlemen pulling out the chair for Emma and then seating herself. Emma fumbled over the menu items that were written in squibbly or some foreign language- ok, maybe it was English but a particularly flooty italicized font, either way- she didn't know what to order.

"Having fun so far?" Regina's voice was so low and seductive Emma couldn't hear her over the roar of blood rushing in her ears. She took her breath away. Emma bit her lip and squinted once more at the menu before confessing in a shameful huff, "I don't know what to order."

"Leave it to me," Regina reassured as the waiter came by to run through the specials.

"I would like the citrus ginger ahi tuna steak, cooked rare, with jasmine rice, and my dear will have the deep sea scallops with linguine. Thank you," Regina winked at Emma when the waiter nodded and exited, "Scallops are like…chicken nuggets of the sea, you'll like them."

Emma believed that she would like them, very much.

_-ok, I'm just improvising this story so smut tomorrow gotta go to sleep after such an exciting day of anon hate and OUAT promo posters and Lana cutie bloopers- so lucky!_


	2. Chapter 2

**A/N: So I wasn't able to get to the "prompted" joys yet, but I wanted to post what I do have written before I go to sleep. You can consider this to be a preview I suppose.**

_Fuck you like a billionaire, Debonair, in my Fred Astaire footwear,_

_Sit back in your chair, come into my lair,_

_bob up for some air, you square, best healthcare.._

_you like it like a tortoise or you like it like a hare? -Peaches, Billionaire_

"The scallops are marinated in an herb and wine cream sauce," Regina studied Emma's face as she tasted them.

"Good," Emma speared another scallop along with some pasta, "They're melty, not too fishy at all. I can't believe you like your fish just seared, practically raw."

"It's delicious, would you like a bite?" Regina leaned forward as she brought her fork up for Emma to taste. Despite the fine dining atmosphere, which would usually make Emma uncomfortable, there was something about being with Regina on this night that relaxed her. Emma was wholeheartedly enjoying the meal, the dim lighting and soft tinkling music increased the intimacy like they were the only two people there. Emma was pleasantly surprised as she took the offered bite off of Regina's fork. Their eyes never left each other until Emma had finished swallowing and went back to her own meal.

Emma studied Regina, her hair and makeup was understated, except for the deep red of her lipstick. The tux she wore was tailored to flatter her feminine shape, and Emma couldn't help but run her eyes over the bow tie at the base of her throat, and down the crisp white pleated shirt with little black buttons, her soft curves plumping the material in all the right places.

In turn, Emma actually felt pretty. Even though she hadn't enjoyed going through the hassle of having professionals do her hair and makeup, she was pleased with the end result. She didn't feel like herself, she felt accentuated, like something more. Feeling bold, she slipped off one of her heels under the table (it was a relief those shoes were pretty but pinchy) she glided her foot up the expensive material of Regina's dress pants and over her calf in the most suggestive way. Regina let out a moan around the mouthful of rice she was currently chewing, and some of their fellow diners turned their heads to see from who the sensual sound came from. Regina's voice had the power to turn a recitation of "The Pledge of Allegiance" into an aphrodisiac.

Emma curtailed the curious looks with a sharp glare of warning, and the patrons turned quickly back to their meals. (Hopefully, they just assumed that the jasmine rice was really damned good). Emma's little move proved successful because now Regina was staring at her like she was doing some serious sexy planning of what she would do to Emma's naked supine body when she had her alone.

Emma no longer felt hungry… (for food), and Regina had already pushed away her plate and placed the napkin on top. Emma didn't even remember the check coming; she just remembered walking blindly through the restaurant and Regina holding the door for her as she exited.

The limo was waiting, and the driver opened the door. Regina moved behind Emma with purpose, grasping her hips and stopping her from getting inside. She ground against the slippery satin covering Emma's ass and she was very well reminded that Regina was packing.

Regina leaned in and whispered in her ear, "you have 30 minutes in this limo to please me however you see fit, and after that you are not permitted to touch me for the rest of the night. It will be my turn to punish or pleasure you as I wish."


	3. Chapter 3

_You got a screw loose, you need a boost to introduce, juiced not seduced, until they tie the noose, never over produced – Peaches Billionaire_

A/N: I guess I like my dates fast and the sex slow because this part takes care of Regina, I'm still working on taking care of Emma…

The limo smelled like new leather, a flashing string of red and blue LED lights ran around the roof, and jazz music softly filtered through the speakers. Emma felt as if she was in another era as she climbed into the spacious back. Regina slid in like a crashing wave, staring expectantly while Emma fumbled with the hem of her dress.

Emma looked her over, feelings burning in her chest. Trust was a big issue for both of them, and it had hampered the level of intimacy in their relationship, and for Regina to offer herself up like this raised the level exceptionally.

"Thirty minutes?" Emma worried about not having enough time to sufficiently please her. It might take that long to get the tuxedo off. Where to begin?

Regina cleared her throat, and produced a gold pocket watch attached to a chain from inside her jacket. She flipped it open and looked at the time. Without looking up, she drawled, "Twenty-nine and a half minutes."

Emma knew Regina's tones well enough, and that meant she was feeling quite eager, so naturally Emma wanted to draw it out and make her wait.

Regina licked her lips and reclined further against the seat, her body language yelled, "Come and take me."

Emma hitched her slinky dress up as the limo began to drive the perimeters of Storybrooke. She slipped her legs over Regina's hips, she wanted to sink down and rub herself against the swell in Regina's pants, but she remained on her knees hovering over her. She knew that's what Regina wanted too and refused to give in just yet. She reached up and toyed with the bowtie, flicking the edge.

The limo ride was smooth as they trekked slowly around Storybrooke, but the outside world needn't bother to exist. Inside, Emma felt like she and Regina were in their own little bubble.

Emma directed her attention to Regina's lips and leaned in, Regina pushed in quickly to meet her, but Emma stopped before they connected. She had a question: "that divider between us and the driver is soundproof right?"

"No," Regina murmured, capturing Emma's lips. They kissed for a moment and Regina tried to wrap her arms around Emma's waist to get her against her, on her, but Emma pulled back with a smack and shrugged Regina away.

"Nuh uh, hands off." Regina obeyed and spread her arms over the seats, opening her body up even more. Emma nipped at her face, whispering between quick adoring kisses, "I love you, I want you, I trust you."

"Em-Ma," Regina husked with a hint of familiar warning. She was making Regina uncomfortable, and Emma felt a little shiver of success. It was rare that they voiced their feelings so explicitly and directly, but Emma wanted to say it. She knew Regina loved it even if she couldn't admit it.

"You said I could please you any way I want, and I just know you crave affection," Emma winked and Regina rolled her eyes, but when they focused back on Emma's they were shining and awash with love.

"How about you sit down on my lap, hmm?" Regina moved her hand to pat her thigh in a tempting invitation.

Emma wrapped her hands around Regina's neck and pressed forward with all her weight, hugging her body tightly, "Oh, but Honey…"

Emma could feel the unamused glare Regina sported at the mention of the sugary term of endearment even as her face pressed awkwardly against Emma's chest. It was so unfitting of Regina, especially in her current attire, Emma couldn't resist and she broke out in a wide smile. She also realized Regina was probably plotting to intensify her punishment by the moment, "…I know whatever you have planned for me tonight will involve a lot of patience on my end, so I just want to give as well as I get."

She kissed Regina sensuously, the genuine smile still upon her lips, and Regina kissed back in earnest. Emma finally relented after what had been only minutes of teasing but Regina acted like Emma was torturing her. She ground her hips down on Regina's lap, shifting and rolling against the bulge she felt there.

"Yesss.." Regina hissed, letting her head fall back against the seat, all the tension leaving her body and going slack as Emma peppered her exposed jaw and neck with more kisses. She loosened the bowtie and worked it apart, moving next to the tiny black buttons on the shirt.

"Have I told you how fucking sexy you look in this?" Emma thrust her hips harder against Regina; she re-situated herself, hiking her dress higher to get more leverage.

"Are you hard for me?" Emma whispered as Regina acknowledged her questions with little groans and breathy gasps. Emma reached between them and cupped Regina roughly, handling her, making sure that the rolled scarf was rubbing against her clit. Regina pulled her close. This time it was she who hugged her taking a deep breath and then relaxing to mold their bodies together. She stroked Emma's hair, rested their foreheads together, and smiled in adoration, "you're beautiful."

Emma crawled off of Regina's thighs slinking down on her knees; she rested her chin on Regina's stomach for a moment, just looking up like a loyal puppy, before adjusting the cummerbund around Regina's waist and finding the buttons on her pants. She brought them down off her hips easily enough. Regina gratefully lifting herself to help, and Emma revealed the tight royal purple boxer briefs beneath.

Emma swallowed, she wasn't expecting that. Regina had really gone all out, and Emma rewarded her by taking the elastic waistband between her teeth and snapping it against her. Emma was happy to note that Regina's toned stomach was quivering slightly. Emma scratched up Regina's thighs, exploring her package while Regina watched quietly, her erratic breath the only physical sign she was giving of her enjoyment.

Emma knew soon enough just how aroused Regina was, when she yanked the boxers down, and found her fake cock darkened with moisture, Emma pushed it aside along with the underwear. A rolled scarf didn't stand a chance against the "stiffer" competition Regina had in her toy box at home, and Emma wanted nothing more than Regina solely as she found the source of her arousal. She tried to spread her legs apart and lift her knee, but the clothes tangled around her legs made it impossible.

Emma simply nuzzled between her thighs and spread her lips with her fingers. She licked lightly, but Regina reacted as if she had been scorched. She was swollen and sensitive and Emma knew just how to take care of her, alternating soft sucks and licks increasing the pressure as Regina grew accustomed to the raw sensations. Emma loved pleasing Regina like this, she chanced a glance at her face, her eyes were shut, her face looking serene like she was basking in the sun. Emma circled her entrance with her tongue and then a finger, swirling just inside where she was most sensitive.

Regina didn't need full penetration to cum, and Emma used her fingers to draw more moisture up over her pussy, long slow strokes alternating with her tongue. Regina lurched forward and reached for the back of Emma's head to pull her closer, a cue for more pressure. Emma obliged willingly, sucking firmly, pushing her finger in a bit deeper. She met no resistance and Regina's hips pushed up off the seat, her back arching as her body struggled for more and more. Emma did prove she certainly could give as she brought Regina up and then slowed her movements, stilling completely refusing to move even as she felt the insistent desperate tug on her head.

Regina let out a short staccato burst of breath, like a sex laden huff of disappointment. Emma waited for a moment before getting back into it and bringing her up to her peak again. She teased her like this until the limo rocked to a stop and Emma knew her play time was up. She had maybe all of 30 seconds before the driver would walk around and open the door.

"Come now," Emma beckoned as she fingered her hard, and sucked her clit deeply. Regina twisted, her nails digging into Emma's scalp, her body twitched as her moan descended into a stifled cry. Emma kissed her pussy once for good measure and pulled away, Regina slumped back in the seat like she was passed out, her pants around her ankles. If only Emma had a camera.

Emma fumbled to bring the tight boxers up, and then the pants, when the swung open, the pants weren't buttoned but at least they were up around Regina's hips and she was mostly decent. The driver didn't even look inside, opting to wait patiently until they made their way out.


	4. Chapter 4

Summary_:_ Anonymous asked you: prompt: swan queen anal sex + toy, packing.

Warnings: See prompt. Mature audiences only, duh. TW: may trigger orgasms. :)

_Hush now baby don't you stress, I'm gonna fill your mommy complex – Peaches_

Emma stretched her legs and followed Regina to her front door. Regina unlocked it and held it open, "Upstairs, wait for my instruction."

Regina had slipped into her disciplinarian mode quickly, but looking so unkempt and fresh-fucked lessened the impact of her orders. Emma bounded up the stairs eagerly and waited in Regina's bedroom. They could have gotten a hotel room to make the night complete but being that Regina's was much nicer than Granny's B&B (aka: "Storybrooke Hilton") was fine with Emma.

She couldn't wait to get out of her dress and heels and into bed. She kept the light off when she entered Regina's bedroom, standing in wait just next to the bed. She was already completely aroused from a mixture of going down on Regina and anticipation of what awaited. Regina stepped into the room carrying drink s. She confidently walked over to Emma looked her over, kissed her lips and handed her a glass of cider.

While Emma took a drink, Regina moved behind her and unzipped the satin dress, slowly pulling it down, letting her fingers linger over her back as she went. Emma raised her arms and as Regina unsnapped her bra. When she was just in her panties, (not a thong, but most of her ass was bare) Regina took her drink, and coaxed her down onto her stomach on the bed. Emma laid still, her arms at her sides, and turned her head to the left against the pillow. She could hear Regina moving around the room, but she couldn't see her.

She didn't feel nervous; she felt relaxed. She absently wondered if her punishment would be painful. Regina loved to torture her by prolonging her pleasure and teasing her, but not giving her release until Emma felt like the air had been knocked out of her and she'd willingly promise Rumplestiltskin a dozen babies if she was just allowed to cum.

She hoped that would be the case. She lost herself in the memory.

Emma heard the sound of clothing shuffling and the click of a latch. When she couldn't see her other senses were heightened, and not knowing what Regina was going to do made her hyperaware for clues. Then Regina kneeled on the bed behind her, bare legs brushing against hers. Hands were skimming the backs of her thighs. Emma felt the fabric of Regina's tuxedo shirt, so she knew that she had removed her pants, but kept her shirt. Emma wanted to turn over and look at her, but she kept still and relaxed letting her curves mold into the soft mattress.

Regina caressed her ass, toying with the slick material of her panties and squeezing her cheeks, pushing and kneading until Emma spread her legs wider. She felt cool air on her pussy, and held her breath in anticipation. Regina held her open, and Emma knew she was studying her. Regina loved to take her time just looking before she made any move to touch her. Emma always felt on display when Regina did this, but she no longer felt embarrassed. She felt revered and admired.

Without warning Regina smacked her ass cheeks, kneading them hard and then striking right and left alternating her hands. The shock of it caused Emma to kick her legs in reflex, but Regina held her down. The rippling sensation bore through her center and the hot sting on her cheeks spread like a wildfire. Regina relented, pausing undoubtedly to admire the red marks she had left. She heard Regina suck in a shuddering breath, and knew something big was next.

Regina stroked the length of her pussy, her finger sliding up her slit and further, her wet fingers danced over Emma's anus, applying the lightest pressure. Emma bristled at the touch. This was new. Regina had never touched her there before. Emma had never been touched like this. It felt different and extremely intimate, and Emma squirmed uncomfortably as Regina pressed firmly with her thumb.

Seeing her apprehension, Regina stopped. She stretched out beside Emma and wrapped her arms around her. She kissed her neck and stroked her hair to soothe her. Emma felt the love and trust emanating from her touch, and sighed contentedly. Whatever Regina wanted to do she knew it was with a strong interest in making Emma feel good and satisfied.

"Will you let me?" Regina spoke in low tones, and Emma gave permission instantly. This was supposed to be her punishment after all; Regina didn't need to ask. Emma had consented for Regina to take her any way she desired. Even when Regina indulged her own need for control and dominance, Emma felt completely cherished. They had a good thing going on, and Emma never had any complaints, just multiple orgasms.

Regina lifted her chin and searched her eyes. Satisfied with what she saw, she kissed her lips and gave her a tip, "Stay relaxed for me."

Regina slid off the bed, and moved around the room, fussing with things, and Emma focused on her breathing. When Regina settled behind her once more, Emma felt more confident and ready. She also felt the tip of a hard plastic cock on her thigh. Then she felt a generous smear of cool lube being applied around her anus. Regina stretched her with her finger, testing her ring of muscles, pressing in until she gave way. Regina was going slow and easy enough that it didn't hurt, it felt nice as the area was sensitive.

"I can't wait to fuck you," Regina delighted in Emma's responsive yet light squirms and shifting hips as her body accommodated the intimate intrusion of Regina's fingers. Emma was sure Regina was going to shove the dildo inside her ass and it was going to be a rude awakening. She'd always thought anal sex would hurt, but so far it was nice. Regina had an uncanny knowledge of Emma's body, and she knew exactly how much Emma could take and what would augment her pleasure.

It was a welcome surprise when Emma felt, not the cock attached to Regina's hips seeking entrance, but something smaller, a tear drop shaped toy. Regina had coated it in lube and then she eased it in, twisting just so until she could let go and the plug stayed in place. Emma stayed still, growing accustomed to the odd feeling of having something up her ass, but the shape and size of the toy was optimal and Emma found she felt full and every movement she made caused a warm blanketing feeling to encompass her nether regions.

Regina checked in with her, and Emma gave the affirmative that was all good, she actually did feel relaxed and Regina seemed to be having fun playing with her body like this. Regina leaned over Emma's back, lying on top of her, covering her body with her own as she rubbed the slick cock against her pussy. She swiveled her hips, causing the dildo to rub slow endorphin releasing circles around and down her cunt, while her belly against Emma's ass made the toy inside her wiggle just a bit, opening her up to new waves of concordant carnality.

Regina greedily searched out Emma's opening and guided the dildo inside, groaning in satisfaction as she ground into her and felt her pussy stretch and take it in. From this angle, flat on her stomach and Regina's weight on top of her, with her pussy and ass stuffed, Emma felt completely filled. She cried out, rubbing her face into the pillow overwhelmed by the feeling. Regina pulled back almost all the way she felt the loss immediately until Regina pushed back in, loving the second plunge just as much as the first.

Going slow and steady, working Emma up and bringing her back down, Regina teased and fucked her with a slow and erratic rhythm. Sometimes pushing in all the way and something giving her short shallow thrusts that hit Emma's g-spot, but it was a hard position to maintain, and Regina felt her lower back strain, her breath was hard to keep even, and her arms quivered from trying to hold herself up. Regina sat back on her knees, urging Emma to lift her ass up, but keep her head down. Emma spread her legs, sticky lube and arousal running down her inner thighs. Regina got up on her knees, pulling her hips close and started to really fuck her.

Emma gasped with each sharp thrust, and Regina no longer worried about being gentle. Emma was hot, her nerve endings crackling and all parts of her ready to receive. Emma pushed back to meet her hips. Regina fucked her harder still, Emma became more animated with her counter movements, crying out louder, partially because it felt good and she couldn't' help herself and partially because she knew Regina loved it when she screamed. Regina held her ass, slapping and jiggling her as she fucked.

Emma was ready to cum; she couldn't wait much longer as she felt her ass squeeze the toy inside, the thin membrane separating the dildo, chugging inside her, from the stationary toy, felt insanely hot. Her pussy was being ravished, and Emma's head buzzed with her intense need, "Come on, harder!"

Regina obliged, intensifying her thrusts. She was panting and squeaking in a way that suggested she was getting close, her pace frantic, and her hands kept slipping off of Emma's ass as she grew distracted by the rush of ecstasy happening between her own legs. In an effort to wring every bit of pleasure from Emma possible, Regina grabbed her trusty little bullet vibrator, turning it up to full blast and rubbing it without warning to Emma's neglected clit.

"Oh, Fuck!" Emma's body acted as if she had been electrocuted, jolting and shaking uncontrollably. The vibrator triggered a huge orgasm that she could feel from the tips of her toes to the top of her head, radiating in a powerful wave like a sonic boom. Her clit was jumping, ass muscles convulsing as she came and came with no end in sight. Regina stole back the vibrator for herself, her hand slipped under her harness and cock to get to her own clit, while the dildo was still buried in Emma's pussy. The beauty of Emma cumming set Regina off, she was so aroused and feeling proud of herself for orchestrating Emma's monumental orgasm. She drew pleasure from giving Emma hers.

Finally, Emma pulled away and spread out on her stomach. She felt thoroughly exhausted, and spent, her pussy dripping cum and lube, her muscles relaxed and sated. Regina cleaned her up with a towel, taking great care to gently remove the anal plug, and wipe her down. Emma muttered her thanks, her numb feeling uncoordinated as if even her face had been affected by her orgasm. Regina slid in next to her, the bedspread was damp with sweat, and Regina kissed Emma's shoulder and cheek. Emma looked up into her eyes, smiling through her fatigue and afterglow haze.

She cradled her face and kissed her lips, and asked teasingly "So when do I get my real punishment?"

"All in good time."


End file.
